Orlando Calderone is the son of deceased drug lord Esteban Calderone, being born to a different mother than his half-sister Angelina Madeira. To ensure Angelina and Orlando were identified as Calderone children, their father gave them each a dolphin gold necklace. Orlando and Angelina were raised in separate homes, and they rarely saw each other.

After the elder Calderone was killed on St. Andrews Island, Orlando began to take over his late father's connections and run his drug empire. Orlando also vowed revenge on the one he felt responsible for Esteban's death--Vice cop Ricardo "Rico" Tubbs, and is particularly incensed that his sister Angelina had Tubbs' love child, Ricardo Tubbs, Jr., and placed a $1 million bounty on Tubbs' head--dead or alive. The bounty nearly got Tubbs and his partner, James "Sonny" Crockett killed in a drug deal gone sour because of their blown cover. Angelina came to Miami to give Tubbs money to escape because she knew Orlando would stop at nothing to get Tubbs, even buying anyone necessary to find him or her. Orlando did buy information from two DEA agents, Walt Harrison and Bill Lyons, and was able to kidnap Angelina and Ricardo, Jr, and take them to the beach. Angelina was tied to her car with explosives (and Orlando took her dolphin necklace and spat on her) set to go off by radio transmitter or if the horn is used, and the baby was taken to the main Calderone house. Orlando barely escaped the SRT barrage after Angelina killed herself in the explosion set off when she hit the horn, and left Tubbs a message at Angelina's and Ricardo Jr's funeral, a card with the dolphin necklace with the warning, "I'll Be Back!"

Nearly one year later, Tubbs bought a lottery ticket from a kid and he won a trip to St. Gerard, an isolated Caribbean island which he took his date, Alicia Austin, on. Once there, he found out the trip was a ruse to get him out of Miami to an area where his badge was worthless, and where Orlando can finish him, once and for all. Orlando brought in his cousin, Xavier Calderone, and "recently paroled" con Leon Wolf that Tubbs recently busted, as backup to get the job done, and paid the police chief and the fishermen not to help Tubbs. But one fisherman, Jacques, gave Tubbs a rifle and used it to kill Xavier, Alicia killed Wolf with Xavier's gun, but Orlando found Alicia and held her hostage, but Tubbs was finally able to kill Orlando (and avenge Angelina's death) and end his vendetta with the Calderones.